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Details

Stereochemistry ACHIRAL
Molecular Formula C29H43N2O4.Br
Molecular Weight 563.567
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OTILONIUM BROMIDE

SMILES

[Br-].CCCCCCCCOC1=CC=CC=C1C(=O)NC2=CC=C(C=C2)C(=O)OCC[N+](C)(CC)CC

InChI

InChIKey=VWZPIJGXYWHBOW-UHFFFAOYSA-N
InChI=1S/C29H42N2O4.BrH/c1-5-8-9-10-11-14-22-34-27-16-13-12-15-26(27)28(32)30-25-19-17-24(18-20-25)29(33)35-23-21-31(4,6-2)7-3;/h12-13,15-20H,5-11,14,21-23H2,1-4H3;1H

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/otilonium-bromide.html | https://www.ncbi.nlm.nih.gov/pubmed/8867109 | https://www.ncbi.nlm.nih.gov/pubmed/25057296

Otilonium is a musculotropic spasmolytic agent belonging to the family of quaternary ammonium derivatives and successfully used in the treatment of patients affected by Irritable bowel syndrome (IBS) due to its specific pharmacokinetic and pharmacodynamic properties. The positive polarity of the head of the Otilonium molecule determines the main pharmacokinetic property of this drug: a minimal systemic absorption and the consequently high safety profile. Studies on animal models revealed a specific Otilonium accumulation in colonic circular muscle at therapeutic µm concentrations, while its plasma levels were 1000 times lower, together with a poor penetration of the drug in the central nervous system. Consistently, after oral administration to healthy volunteers, the Otilonium plasmatic concentration was very low, less than 1% of the drug was eliminated by urine, and 97% was eliminated by feces. Recent clinical studies showed comparable safety and tolerability for Otilonium and placebo. Otilonium was shown to inhibit the main patterns of human sigmoid motility in vitro, including: the tone of smooth muscle cells (SMCs); the rhythmic phasic contractions induced by the interstitial cells of Cajal; and the strong contractions induced by stimulation of enteric motor neurons mainly by blocking the calcium influx through L-type calcium channels on SMCs. Recent in vitro studies using cultured human colonic SMCs to further assess the musculotropic spasmolytic properties of Otilonium confirmed that this drug causes smooth muscle relaxation through the inhibition of voltage-gated calcium channels (L-type > T-type) and the inhibition of muscarinic and tachykinergic effects.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Obimal

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Multicenter phase III clinical trial of otilonium bromide in irritable bowel syndrome.
2002 Mar-Apr
Irritable bowel syndrome.
2007
Effect of otilonium bromide on contractile patterns in the human sigmoid colon.
2010 Jun
Patents

Patents

Sample Use Guides

3 tablets (3 × 40 mg) daily before meals (120 mg Otilonium/day)
Route of Administration: Oral
Human circular smooth muscle cells were used for activity evaluation. To determine the effect of Otilonium on ionic conductances in human jejunal circular smooth muscle, we patch clamped enzymatically dissociated cells with Cs+ in the pipette to block outward K+ currents and with NaCl or NMDG-Cl Ringer’s extracellular solution. Electrodes were coated with R6101 (Dow Corning, Midland, MI, USA) and fire polished to a final resistance of 3–5 M. Currents were amplified, digitized and processed using an Axopatch 200B amplifier, a Digidata 1200, and pCLAMP 8 software (Axon Instruments, Foster City, CA, USA). In experiments examining Na+ or Ca2+ current, whole cell records were sampled at 10 kHz and filtered at 4 kHz with an eight-pole Bessel filter. For these experiments, cells were held at -100 mV and pulsed from -80 to +35 mV in 5 mV intervals for 50 ms. Otilonium (0.09–9 mkM) was used as this reproduced clinical intracellular concentrations. In human circular smooth muscle cells, Otilonium inhibited L-type Ca2+ current by 25% at 0.9 mkM and 90% at 9 mkM.
Name Type Language
OTILONIUM BROMIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
DIETHYL(2-HYDROXYETHYL)METHYLAMMONIUM BROMIDE P-(O-(OCTYLOXY)BENZAMIDO)-BENZOATE
Common Name English
SP63
Code English
otilonium bromide [INN]
Common Name English
OCTYLONIUM BROMIDE
Common Name English
DORALIN
Brand Name English
OTILONIUM BROMIDE [MART.]
Common Name English
OTILONIUM BROMIDE [MI]
Common Name English
SPASMOCTYL 40
Brand Name English
SP-63
Code English
Otilonium bromide [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
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WHO-VATC QA03AB06
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WHO-VATC QA03CA04
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WHO-ATC A03CA04
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WHO-ATC A03AB06
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Code System Code Type Description
MESH
C013934
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PRIMARY
ECHA (EC/EINECS)
247-457-4
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DRUG CENTRAL
2003
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WIKIPEDIA
Otilonium bromide
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FDA UNII
21HN3N72PV
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EVMPD
SUB09479MIG
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RXCUI
54216
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PUBCHEM
72092
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INN
4325
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MERCK INDEX
m8267
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DRUG BANK
DBSALT002518
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EPA CompTox
DTXSID0046357
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CAS
26095-59-0
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ChEMBL
CHEMBL1433361
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NCI_THESAURUS
C90743
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SMS_ID
100000083575
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